145438-94-4

Basic information

• Product Name: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid
• Synonyms: Trandolapril Bicyclic Acid;(2S,3aR,7aS)-octahydroindolecarboxylic acid;1H-Indole-2-carboxylicacid, octahydro-, (2S,3αR,7αS)-;Perindopril Related Compound 1;(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid;L-Octahydroindole-2-carboxylic acid;L-Octahydro-1H-indole-2-carboxylic acid;Trandolapril Intermediate 1
• CAS NO: 145438-94-4
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.22
• EINECS: 1312995-182-4
• Product Categories: Heterocycles;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 145438-94-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 307-309?C (dec.)
• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: White crystalline solid
• Density: 1.135 g/cm³
• Vapor Pressure: 7.54E-05mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated, Sonicated), Methanol (Sparingly, Heated, Sonicated), Wat
• PKA: 2.47±0.20(Predicted)
• CAS DataBase Reference: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid(145438-94-4)
• EPA Substance Registry System: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid(145438-94-4)

Safety Data

• Hazardous Substances Data: 145438-94-4(Hazardous Substances Data)

Usage

Description

(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid is an organic compound with a unique molecular structure characterized by its octahydroindole framework and carboxylic acid functional group. It is a white crystalline solid, which indicates its stable and solid-state physical properties.

Uses

Used in Pharmaceutical Industry:
(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid is used as a Trandolapril intermediate for the synthesis of Trandolapril, an angiotensin-converting enzyme (ACE) inhibitor. Trandolapril is a medication used to treat high blood pressure and heart failure. The compound's role as an intermediate in the production of this drug highlights its importance in the pharmaceutical industry for developing life-saving medications.
As a Trandolapril intermediate, (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid plays a crucial role in the chemical synthesis process, contributing to the development of a drug that helps manage cardiovascular conditions. Its chemical properties, including its white crystalline solid state, make it suitable for use in the synthesis of pharmaceutical compounds.

InChI:InChI=1/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7+,8+/m1/s1

Upstream product

• 87624-03-1 (4aR,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 87623-95-8 (2R,3aS,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 89226-35-7 N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclohexyl]-acetamide 
• 59224-99-6 trans-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 79799-08-9 (2S,3aS,7aS)-Octahydro-indole-2-carboxylic acid ethyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 3770-50-1 2-carbethoxyindole 
• 4169-27-1 cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 87623-95-8 (2S,3aR,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 120-72-9 indole 
• 87623-93-6 (3aR,7aR)-1-(Octahydro-indol-1-yl)-ethanone 
• 1193-68-6 cis-octahydroindole 
• 144540-71-6 (2S,3aR,7aS-octahydroindole)-2-carboxylic acid-benzyl ester 

Downstream Products

• 108395-25-1 (2α,3aβ,7aβ)-1-(3-bromobenzoyl)octahydro-1H-indole-2-carboxylic acid 
• 80828-12-2 (2R,3aR,7aR)-1-(3-Acetylsulfanyl-propionyl)-octahydro-indole-2-carboxylic acid 
• 80828-31-5 (2α,3aβ,7aβ)-1-benzoyloctahydro-1H-indole-2-carboxylic acid 
• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid 1,1-dimethylethyl ester 
• 82717-91-7 (+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt 
• 1555994-20-1 (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-22-3 (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-24-5 (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol 
• 1555994-26-7 (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-29-0 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-31-4 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1609090-02-9 C₂₀H₂₈NO₉P 
• 87679-37-6 trandolapril 

Relevant articles and documents

The synthesis of trans-perhydroindolic acids and their application in asymmetric domino reactions of aldehyde esters with β,γ-unsaturated α-keto esters

(2S,3aR,7aS)-Perhydroindolic acid, the key intermediate in the synthesis of trandolapril, and its trans-isomers, were readily prepared. These proline-like molecules are unique in that they contain a rigid bicyclic structure, with two hydrogen atoms trans to each other at the bridgehead carbon atoms. These molecules were used successfully as chiral organocatalysts in asymmetric domino Michael addition/cyclization reactions of aldehyde esters with β,γ-unsaturated α-keto esters. They proved to have excellent catalytic behavior, allowing for the synthesis of multi-substituted, enantiomerically enriched hemiacetal esters. Under optimal conditions (using 10 mol% catalyst loading), a series of β,γ-unsaturated α-keto esters was examined with up to 99% de, ee and yield, respectively. Additionally, the enantiomerically enriched hemiacetal esters could be readily transformed into their corresponding bioactive pyrano[2,3-b]pyrans (possessing a multi-substituted bicyclic backbone). Copyright

PROCESS FOR THE SYNTHESIS OF AN ACE INHIBITOR

A process for the synthesis of trandolapril which comprises condensing N-[I-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride with trans octahydro-1H- indole-2-carboxylic acid in a first organic solvent comprising a water immiscible inert organic solvent and in the presence of a base, and isolating trandolapril from a second organic solvent. N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride may also be condensed with (2S,3aR,7aS) octahydro-1H-indole-2-carboxyIic acid in a first organic solvent and in the presence of a base, and trandolapril isolated. There is also provided a process for the resolution of racemic trans octahydro-1H-indole-2-carboxylc acid.

Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids

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